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C0225000

Calcitriol

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

1α,25-Dihydroxyvitamin D3, 1α,25-Dihydroxycholecalciferol, Calcitriol

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About This Item

Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
Molecular Weight:
416.64
Beilstein:
7559394
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

biological source

sheep wool (grease)

grade

pharmaceutical primary standard

Agency

EP

API family

calcitriol

form

solid

manufacturer/tradename

EDQM

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

−20°C

SMILES string

[H][C@@]1(CC[C@@]2([H])C(\CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)CCCC(C)(C)O

InChI

1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1

InChI key

GMRQFYUYWCNGIN-NKMMMXOESA-N

Gene Information

human ... VDR(7421)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the authority of the issuing pharmacopoeia. For further information and support please go to the website of the issuing pharmacopoeia.

Calcitriol is a biologically active metabolite of vitamin D, formed via hydroxylation of calcidiol in the kidney.

Application

Calcitriol EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - STOT RE 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Optimization of culture conditions for transformation of vitamin D3 to calcitriol by Actinomyces hyovaginalis isolate A11-2
Abbas MA, et al.
Archives of Clinical Microbiology, 2(6) (2011)
Beth J Kirby et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 28(9), 1987-2000 (2013-03-19)
Pregnancy invokes a doubling of intestinal calcium absorption whereas lactation programs skeletal resorption to provide calcium to milk. Postweaning bone formation restores the skeleton's bone mineral content (BMC), but the factors that regulate this are not established. We used Pth-null
Ryoko Okamoto et al.
International journal of cancer, 134(1), 207-217 (2013-06-19)
We have synthesized 39 1,25-dihydroxyvitamin D3 [1,25(OH)2D3] analogs having two side chains attached to carbon-20 (Gemini) with various modifications and compared their anticancer activities. Five structure-function rules emerged to identify analogs with enhanced anticancer activity. One of these active analogs
Ichiaki Ito et al.
The Journal of clinical investigation, 123(11), 4579-4594 (2013-10-19)
The TGF-β superfamily comprises pleiotropic cytokines that regulate SMAD and non-SMAD signaling. TGF-β-SMAD signal transduction is known to be involved in tissue fibrosis, including renal fibrosis. Here, we found that 1,25-dihydroxyvitamin D3-bound [1,25(OH)2D3-bound] vitamin D receptor (VDR) specifically inhibits TGF-β-SMAD
Edwin C Y Chow et al.
American journal of physiology. Endocrinology and metabolism, 304(9), E977-E989 (2013-03-14)
The vitamin D receptor (VDR) maintains a balance of plasma calcium and 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3], its natural active ligand, by directly regulating the calcium ion channel (TRPV6) and degradation enzyme (CYP24A1), and indirectly regulating the parathyroid hormone (PTH) for feedback

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